TY - JOUR
T1 - Direct catalytic asymmetric addition of allyl cyanide to ketones
AU - Yazaki, Ryo
AU - Kumagai, Naoya
AU - Shibasaki, Masakatsu
PY - 2009/3/11
Y1 - 2009/3/11
N2 - A direct catalytic asymmetric addition of allyl cyanide to ketones with a bimetallic catalytic system comprising (R,R)-Ph-BPE/[Cu(CH3CN) 4]ClO4/LiOAr is described. Exclusive γ-addition of allyl cyanide was observed, affording optically enriched tertiary alcohols bearing Z-configured α,ß-unsaturated nitriles. The reaction proceeded under proton-transfer conditions, utilizing soft Lewis acid/hard Brønsted base bifunctional catalysis. The applicability of the reaction to aromatic, heteroaromatic, and aliphatic ketones demonstrates its wide substrate generality.
AB - A direct catalytic asymmetric addition of allyl cyanide to ketones with a bimetallic catalytic system comprising (R,R)-Ph-BPE/[Cu(CH3CN) 4]ClO4/LiOAr is described. Exclusive γ-addition of allyl cyanide was observed, affording optically enriched tertiary alcohols bearing Z-configured α,ß-unsaturated nitriles. The reaction proceeded under proton-transfer conditions, utilizing soft Lewis acid/hard Brønsted base bifunctional catalysis. The applicability of the reaction to aromatic, heteroaromatic, and aliphatic ketones demonstrates its wide substrate generality.
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U2 - 10.1021/ja900001u
DO - 10.1021/ja900001u
M3 - Article
C2 - 19215140
AN - SCOPUS:70349938534
SN - 0002-7863
VL - 131
SP - 3195
EP - 3197
JO - Journal of the American Chemical Society
JF - Journal of the American Chemical Society
IS - 9
ER -